5-7 Days in Tuscany with a Family of 5 with Adult-aged Kids

[elenagc0604]

Hi! Need any and all advice on planning a trip to Tuscany for my family in Summer 2026.

We're a family of 5- my parents, me (26), my sister (29), and her boyfriend (30). This is not my first time in Italy, but it is for the rest of the group. We are thinking of starting in Lake Como/Bellagio for a few days, and then we'd hit Tuscany (or the other way around depending on logistics).

We're hoping to see some historical sites, but nothing too touristy, and mainly see some vineyards, have good food, and experience the culture. Can anyone recommend a good place to stay as our home base with some day trips that are easily accessible? Something that is kind of central to other good areas and offers different things to do?

Thank you!!

 

[Lourdes]

Ciao ElenaGC,

What you have outlined sounds like a great plan for your family's vacation in Italy! Do you already have an idea of the total number of days you will have overall or at least in Tuscany?

I ask solely because in the high season, mainly in the summer (but some places determine this as covering various months, from May/June through end of August/September), some accommodations in the countryside set the rule that they will accept only weekly stays and not by the night. Those are mainly the agriturismos or farmhouses that have apartments and they rent them by the week. That means that in searching for a place you like, you will find many places you like that might have this requirement. So you might have to extend the days you were in Tuscany if you had planned for less days.

The other consideration is whether you plan to rent a car and drive while in Italy. It will determine a great deal the options you have as to where to stay. If you want to stay out in the countryside in Tuscany, then a car is almost a requirement. But it doesn't mean you have to drive - there are some places in Florence and Siena, for example, that are right on the outskirts that can make you feel like you're on a farm stay, but have the convenience of local buses back into town from which you can take the train to do day trips. If you want to visit wineries in that case, I'd recommend joining some wine tours, which have the advantage of someone else driving you around so that all of you can actually do wine tasting and drinking.

So good areas that are central and perfect for day trips are Florence and Siena for sure, like I mentioned above, where a car might not be needed at all, then Chianti (area between Florence and Siena) since it will have you in the heart of wine country, as well as the Val d'Orcia and Montalcino (areas to the south of Siena), to be in more wine country. All these areas have loads of wineries as well as great local restaurants with delicious food and many small villages and towns that will make exploring a wonderful experience. You can set out each day in a different direction and stop where you want, as everything has its charm. You can search through this forum for more ideas of specific itineraries or through the main sites and you will find suggested itineraries through all of these areas.

 

[Lourdes]

Ciao Elena GC,

I was thinking of less touristy areas for your base.

I want to add that the Mugello area to the north of Florence sometimes gets overlooked but it is close enough to Florence and Chianti that it makes a good base, while also being less touristy and thus less crowded. Maremma also is a great area to stay in that is not too touristy, as long as you're not visiting at the height of the summer beach months, as then the coastal area does get crowded. If you go inland, not as crowded but this really depends on when you're planning on coming.
Another area that is often overlooked in the hills between Pisa and Lucca called the Montepisano. Lots of small villages and easy to use as a base, and again, the sea and beaches are not far away, but depends on when your family trip is planned for. This local tour operator (https://www.montepisano.travel/) has itineraries and packages for the area.

Let me know what you're looking into and if you want specific recommendations for places to consider in some of these areas, if you have some idea of what you're looking for.